


First Dates

by chucks_prophet



Category: Supernatural
Genre: Anna is a good sister, Castiel and Anna Milton are Siblings, Castiel is cute, Dean is a Sweetheart, First Dates, Fluff, High School Castiel/Dean Winchester, Humor, If You Couldn't Tell By The Title ;P, Implied Sexual Content, Implied/Referenced Sex, M/M, Making Out, Minor Anna Milton/Dean Winchester, Protective Castiel, Sex in the Impala, Sexual Humor, Tooth-Rotting Fluff, Unrequited Crush, no actual sex though
Language: English
Status: Completed
Published: 2017-04-19
Updated: 2017-04-19
Packaged: 2018-10-21 02:05:12
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,549
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10675443
Author URL: https://archiveofourown.org/users/chucks_prophet/pseuds/chucks_prophet
Summary: “What?” Anna can feel the heat rise to her chest like a pie left a little too long in the oven. If there’s one thing she hates more than Cas not owning up to his promises, it’s him playing dumb about them. “I’m not following you.”“Oh really?” she argues, crossing her arms. “Why are you trying to cut in front of me then?”The doorbell chimes again before she can pry an answer out of him. Anna rolls her eyes and heads for the door, trying to ignore the extra foot looming over her as she opens it.





	First Dates

**Author's Note:**

> Inspired by a video on "awesomeness"'s IG entitled, "Trying to date when you have an older brother", with my own spin on it.

First Dates

_"Are you serious?!"_ Anna rages as she walks into the bathroom, shared with her seventeen-year-old brother.

Anna Milton needs her older brother, Castiel.

Sometimes.

Sometimes, she needs help with her reading homework without the judgment from their parents. Other times, she needs him to hold her hair when she stays out an hour too late and comes home one more sheet to the wind than necessary. Sometimes, she even needs help  _doing_ her hair, because Cas knows how to do a wicked French braid for their little sister, Hael, who’s obsessed with  _Frozen._

Except right now. She certainly doesn't need him, just like her prospective boyfriend doesn't need a glimpse of what life is going to be like with Cas hovering over him like a blimp on their first date. Seriously, ever since going on her first outing last year, Anna’s dates have been subjected to Cas’s hardnosed stares and rigorous round of 20 Questions at their doorstep, and even the occasional chaperoning that Cas uses as an excuse because he’s been dying to see the latest romcom at got a whopping 42% on Rotten Tomatoes.

(And then when her dates bail, Cas just shrugs and says, “If he scares away that easy, he’s not ready for his commitment to you and our family.”)

"What?” Cas says, turning around briefly from threading his fingers through his messy brown hair. “Can't we use the bathroom at the same time?"

Anna shakes her head as she pushes Cas away from the sink. "Absolutely not. You're up to some—are you wearing cologne???”

"I believe it's called the Axe effect,” Cas, high school senior with dual enrollment credits in Sass and Sequential Arts, snarks. He even cocks his head a little into the side mirror as he says it, but doesn’t stop fixing his hair.

"I know what it is, I just—what are you doing with your hair?!”

Cas shrugs. "Maybe I don't want to look like I just rolled out of bed. Why are you all huffy?"

"I’m not huffy,” Anna says. She snatches her makeup bag from her side of the counter and rummages inside until she finds her eyeliner. She eyes herself in the mirror as she uncaps the lid, breathing in deep to expand her chest. Her auburn red hair needs a little more volume (so does her chest, but it’s nothing a crop top can’t fix) the way it falls to her sides like printing paper coming through the shredder, but mousse will help with that. Aside from that, everything looks alright.

And alright can be fixed with makeup, so no worries there.

"I'm pretty sure you are,” Cas scoffs, adjusting the turndown collar on his blue long sleeve. It’s not out of character for him, this clothing. Considering his habitual suit and trench coat he wears that makes him look even more menacing to her dates, it’s just different attire. And it brings out his eyes more than the faded blue tie he usually wears around his neck—that’s what makes her even more suspicious.

"Stop creeping out my dates," she says, making a point to meet his eyes in the mirror. "I'm sixteen."

"Do you ever think maybe  _I'm_  the one going out on a date?"

Anna pauses from applying her eyeliner to look up at Cas with a less evenly applied smile. "You're cute."

"Fine,” Cas concedes as Anna starts to apply her mascara next, holding up his hands.

If Anna could narrow her eyes, she would. "Really? Just like that?"

"Just like that," Cas says. "You're right. You're sixteen; you're fully capable of making the right decisions.”

Anna blinks a few times, partially from the mascara, and then faces Cas with a small smile. "Thank you."

"You're welcome." A beat, and then, as Anna pulls out her tweezers, Cas adds:  "What are you doing, anyway?"

"One day, you'll know the pain in beauty."

"One day?"

"Yeah," Anna says, "We  _have_  to fix your eyebrows one of these days."

"What's wrong with my eyebrows?" Cas asks.

"They need shape."

"Funny, because April told me I had  _plenty_  of shape last time we—”

"Ugh, gross," Anna groans, shoving Cas lightly. Cas just chuckles in that older-evil-brother sort of way as the doorbell chimes downstairs. Anna bounces in her step as she announces, "That's my cue."

Only, Anna’s in close competition to Cas when she races down the stairs, and even when Anna gives him  _that_ glare, Cas’s eyebrows taper. “What?” Anna can feel the heat rise to her chest like a pie left a little too long in the oven. If there’s one thing she hates more than Cas not owning up to his promises, it’s him playing dumb about them. “I’m not following you.”

“Oh really?” she argues, crossing her arms. “Why are you trying to cut in front of me then?”

The doorbell chimes again before she can pry an answer out of him. Anna rolls her eyes and heads for the door, trying to ignore the extra foot looming over her as she opens it.

“Dean, you caught me by surprise,” she says, putting on her best smile. “I’m barely made up.”

Dean, however, is completely made up. He’s wearing a blue long sleeve, similar to Cas’s, only he’s sporting a black tie over it and a leather jacket over  _that_ , paired with blue jeans that nicely show off his bowlegs and cut off just before his trademark brown boots. He’s freshly ridden of his ginger stubble, making his big, nibble-worthy lips stick out more than usual, his forest-green eyes pop from the—wait, is that a hint of eyeliner??? And judging by the shininess in his dark caramel hair that’s up in a fine point, he’s even wearing gel.

Dean smiles. “You look great as always, Anna. You ready, Cas?”

Anna’s smile wipes from her face quicker than Dean can thrust the hydrangeas in his hands at Cas.

Cas accepts the bouquet with a blush and a loss for words. Dean’s smile amplifies by x1000 as he lends out his hand. Cas is hesitant at first, but then extends his own and weaves their fingers together with the carefulness of a spider building a web. Once Cas steps outside the frame, he closes the distance between their hands, so they walk down the driveway hand-in-hand.

Anna crosses her arms over her chest as she watches Dean’s ’67 Chevy drive off. As much as she wants to be mad at the loss of a date with a  _really_ hot senior, she can’t help the smile that returns to her face: After this whole year looking after Anna, maybe it’s Cas’s turn to experience something good in his life.

 That, and at least if Cas gets laid, with any luck, he’ll be less of a smartass.

**BONUS:**

“Do you think Anna thought her and I were going on a date?” Dean asks.

“I think,” Cas says in-between hungry hickeys, “my sister can leave a message after the tone.”

However, guilt consumes him as soon as he hears the words come out, and Cas unlatches his mouth from Dean’s neck and sits up. As much as he wants to complain about the lack of contact, he can’t help drinking in how beautiful Dean looks like this.

He’s still fully-clothed, but his legs are spread out on the long line of leather supporting their combined weight. His pants are hanging off rather than hugging his hips, with just enough modesty to let Cas’s imagination run wild. His sleeves are bunched up around his strong arms and looser around the collar, showing off Cas’s handy work. Above that are Dean’s green eyes, which are inflated with lust, and don’t deflate even for the heavy breaths spilling from his large, pink lips.

Cas sighs. Damn her. “She may have… overheard our conversation we had after school.”

“What?” Dean says, sitting up a little, “I mean, even if she did, I asked  _you_ out.”

“Technically you asked out ’the most beautiful Milton at Kansas High’.”

“So?”

“So,” Cas continues, “she’s sixteen. She wants to believe that she’s the best thing, and I didn’t have the heart to… I don’t know. What?”

Dean graces Cas with a look he can’t quite decipher, then smiles and glides his hands resting on Cas’s hips up to his chest. “Nothing. You’re just amazing. And really hot.”

“What happened to me being beautiful?” Cas teases.

“The state of being hot is temporary,” Dean explains, and Cas isn’t sure if he follows already, it’s probably more or less due to the lack of blood flow being caused by his downstairs brain, but he lets him continue with that goofy half-grin Dean does when he’s building to a point, “but the state of being beautiful, that’s forever.”

“Mmm, so I’m both?” Cas laughs and lets himself be guided so they’re reversed, and he’s underneath Dean.

“If you wanna be cocky about it, sure,” Dean says, dragging his thumb over Cas’s bottom lip. “To be fair, you still have to prove your sexiness. That’s an entirely different category.”

“What’s my time frame there?” Cas asks, playing along.

Dean responds by peeling off his shirt and saying, “However long it takes you to get undressed.”

Cas has never reached for his shirt buttons faster.


End file.
